Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D213/72—Nitrogen atoms
  • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals

Definitions

• the invention relates to new N-pyridyl-forrnimino ethers of valuable therapeutic effects, as well as to a process for the preparation of such N-pyridyl-formimino. ethers.
• the new compounds of the present invention can be characterized by the formula wherein R represents a saturated straight or branched chain alkyl group of 7 to 16 carbon atoms, a cycloalkyl group of 5 to 6 carbon atoms, a benzyl or phenylethyl group or a dimethylaminoethyl or diethylaminoethyl radical and R represents hydrogen, halogen, nitro or lower alkyl.
• the N-pyridyl-formimino ethers of Formula I can be prepared according to the present invention by reacting a formimino-alkyl ether of the formula wherein X represents an alkyl group of 1 to 4 carbon atoms, and R has the same meaning as above, with an alcohol of the formula HOR (III) wherein R has the same meaning as above.
• This reaction can be performed preferably in the presence of an organic solvent, and of an alkali metal or an alkali alkoxide.
• the alcohol of Formula III may be used in an equimolecular amount or, more preferably, in excess; the reaction proceeds in general readily at the reflux temperature of the reaction mixture.
• the obtained N-pyridyl-formimino ethers of Formula I may be converted in known manner, if desired, into quaternary ammonium derivatives.
• the new compounds of the present invention show a potent and selective anthelmintic action against well developed worms of the species Tubifex rivularium.
• the anthelmintic elfects of the new compounds are stronger than those of the anthelmintic agents known and used hitherto.
• the new compounds also show a cercaricidal activity, which is unusual for anthelmintics.
• EXAMPLE 1 The mixture of 12.5 g. (0.0832 mol.) of N-(4-pyridyl)- formimino-ethyl ether and 21.6 g. (0.2 mol.) benzyl alcohol was heated in the presence of 0.05 g. of metallic sodium for two hours at -120 C. The ethanol formed during the reaction was distilled off continuously; the end of the reaction was shown by collecting of the theoretical amount of ethanol in the distillate. The distillation residue was then fractionated; the obtained N-(4-pyridyl)-formimino-benzyl ether boils under 0.1 mm. Hg at 70-78 C.
• N- Zmeihyl-Z-pyridyl) -formimino-octylether-- EXAMPLE 3 The mixture of 150.18 g. (1 mol.) of N-(3-pyridyl)- formimino-ethyl ether and 242.4 g. (1 mol.) of cetyl alcohol was dissolved in 500 ml. of benzene. The solution was then heated to the boiling point and the formed ethanol was distilled off as an azeotropic mixture with benzene. At the end of the reaction the benzene was distilled oif too, and the residue was subjected to fractionated distillation. The obtained N-(3-pyridyl)formimino cetyl ether boils under 0.05 mm. Hg at 193195 C. The following additional compounds have also been prepared by the method of the above example:
• EXAMPLE 6 The mixture of 150.18 g. (1 mol.) of N-(2-pyridyl)- formimino ethyl ether and 122.16 g. (1 mol.) of ,8-phenyl ethyl alcohol in 600 ml. of toluene was heated at 110- 140 C. for three hours in the presence of 0.05 g. of metallic sodium. The product was isolated as described in Example 2; the obtained N-(2-pyridyl)-formimino phenyl-ethyl ether boils under 0.05 mm. Hg at 135 C.
• Table II shows similar minimal inhibiting concentrations in mg. percent, compared with those of three wellknown anthelmintic agents.
• N-(3-pyridyl)-formimino-cetyletl1er 15. 5-31 3. 5-7.
• N-(2-pyridyl)-formimino-cyelopentyl-ether 15. 5-31 15.
• 5 N-(5-chloro-2pyridyl)-formimino-4 -heptylether 15. 5-7. 5 7. 5 Known compounds for comparison:
• N-(5-chloro-2- pyridyl)-formimino ethyl ether 11.62 g. (0.1 mol.) of heptan-4-ol and 0.1 g. of metallic sodium was reacted as described in Example 2.
• the obtained N-(5-chloro-2- pyridyl)-formimino 4'-heptyl ether boils under 0.05 mm. Hg at 162182 C.
• the following additional compounds have also been prepared by the method of the above example:
• R is a member selected from the group consisting of hydrogen, halogen, nitro and lower alkyl.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Pyridine Compounds (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Applications Claiming Priority (2)

Publications (1)

Family

ID=26318444

Family Applications (1)

Country Status (8)

Cited By (3)

Families Citing this family (2)

• 1968
  • 1968-03-28 GB GB05049/68A patent/GB1192995A/en not_active Expired
  • 1968-04-08 DE DE1770156A patent/DE1770156C3/de not_active Expired
  • 1968-04-08 FR FR1565762D patent/FR1565762A/fr not_active Expired
  • 1968-04-09 DK DK158168AA patent/DK118558B/da unknown
  • 1968-04-09 NL NL6805020A patent/NL6805020A/xx unknown
  • 1968-04-10 SE SE04914/68A patent/SE347742B/xx unknown
  • 1968-04-11 CS CS2699A patent/CS151467B2/cs unknown
• 1970
  • 1970-04-21 US US30591A patent/US3590037A/en not_active Expired - Lifetime

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